Hydrogen Bromide → 4-(1H-benzimidazol-2-yl)[1,4]diazepane hydrobromic acid salt

HRID 637088Notes

Reaction equation

HRID 637088 reaction equation
C(OC([N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]=2)[CH2:8][CH2:7]1)=O)C.[BrH:22]>C(O)C>[BrH:22].[NH:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[N:9]1[CH2:10][CH2:11][CH2:12][NH:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 184650911-ethoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane

Product 1

HCID 698342994-(1H-benzimidazol-2-yl)[1,4]diazepane hydrobromic acid salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 1-ethoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepane (5.22 g, 18.1 mmol) and aqueous 48% hydrobromic acid solution (25 mL). Heat to reflux. After 4 hours, cool to ambient temperature and concentrate in vacuo to give a residue. Combine the residue and ethanol (150 mL). Evaporate in vacuo to a volume of about 75 mL and cool to give a solid. Collect solid by filtration, rinse with ethanol and then diethyl ether, and dry in vacuo to give 4-(1H-benzimidazol-2-yl)[1,4]diazepane hydrobromic acid salt. Elemental Analysis calculated for C12H16N4.2HBr: C, 38.12; H, 4.80; N, 14.82. Found: C, 38.17; H, 4.84; N, 14.60.

Workup

  1. temperatureHeat to reflux
  2. concentrationconcentrate in vacuo
  3. customto give a residue
  4. customEvaporate in vacuo to a volume of about 75 mL
  5. temperaturecool
  6. customto give a solid
  7. customCollect solid
  8. filtrationby filtration
  9. washrinse with ethanol
  10. dry with materialdiethyl ether, and dry in vacuo

Sources & evidence

ORD record
ord-7fa405688d0443ce8863614e8f4c154b
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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